Synthesis of a thiophene-fused isoindigo derivative: a potential building block for organic semiconductors

Zhao, Na; Qiu, Li; Wang, Xiao; An, Zengjian; Wan, Xin

doi:10.1016/j.tetlet.2013.12.076

Cited by 18 publications

(11 citation statements)

References 33 publications

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“…The starting material 2-bromo-5-nitrobenzo[b]thiophene (5) was synthesized according to the literature. 29,30 Following the similar procedure to previously reported ones, 14 α,α′-dibrominated TII (11) was synthesized.…”

Section: Methodsmentioning

confidence: 95%

“…13 Inspired by this report, we synthesized thiophene-fused isoindigo (as shown in Scheme 1b) and disclosed its photophysical and electrochemical properties, showing that the intramolecular charge transfer was enhanced due to the extension of the π-conjugated system. 14 Further extension of the π-conjugated system (benzothiophene-fused isoindigo and benzofuran-fused isoindigo, Scheme 1c and d) led to small molecular OFETs with electron mobility up to 0.074 cm 2 V −1 s −1 under ambient conditions. 15 More recently, similar modifications on the isoindigo core were also reported (Scheme 1e-g) including thieno [3,2-b]thiophene isoindigo, 16 benzothienoisoindigo, 17 and thieno [3,2-b]- [1]benzothiophene isoindigo.…”

Section: Introductionmentioning

confidence: 99%

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Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

Zhao

Cai

et al. 2016

Polym. Chem.

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A series of donor-acceptor (D-A) type conjugated polymers based on novel thiophene-fused isoindigo (TII) were designed and synthesized via palladium catalyzed Stille copolymerization. We found that the redesign of the synthesis of brominated TII was necessary, and the α-bromination had to be completed at the very beginning, or β-brominated TII was obtained, which only led to cross conjugated polymers.Once the bromination was introduced at the correct position, fully conjugated D-A type polymers could be obtained. A series of fully conjugated polymers were obtained by Stille coupling polymerization of α-brominated TII with different donors, and among them, copolymers with thiophene (T) and (E)-1,2-bis (3-octylthiophen-2-yl)ethene (TVT-8) showed acceptable solubility and were suitable to fabricate solution-processable organic field-effect transistors (OFETs). Top-gate/bottom-contact (TG/BC) devices were constructed for the polymers to test their OFET performances. Both fully conjugated polymers exhibit two-orders of magnitude higher charge carrier mobilities than the cross conjugated ones, and PTII-T shows balanced electron and hole mobilities and PTII-TVT-8 is a p-type dominated semiconductor. These observations indicated that the developed TII unit that has improved coplanarity can be a promising building block for the construction of highly efficient conjugated polymers for OFET applications.

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Section: Methodsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

Zhao

Cai

et al. 2016

Polym. Chem.

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“…Inspiringly, the alkylation and condensation are carried out in a one‐pot reaction in this method (Figure 1g). [ 54 ] In addition to constructing the center double bond, constructing the amide bonds is an alternative tactic. Xu and co‐workers reported method h for synthesizing thienoisoindigo.…”

Section: Synthetic Tactics Of Isoindigo‐derived Monomers and Polymersmentioning

confidence: 99%

“…The monomer showed lower LUMO energy level compared to isoindigo due to the extended π‐conjugated system. [ 54 ] M21 ‐based P42 exhibited ambipolar transport with hole and electron mobilities of 0.018 and 0.029 cm 2 V −1 s −1 , respectively (Figure 6c). The low mobilities were attributed to the relatively low molecular weight.…”

Section: Modification Strategies Of Isoindigo‐derived Polymer For Ofetsmentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

Zhang

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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“…Previously, our group synthesized thiophenefused isoindigo (as shown in Scheme 1) and disclosed its photophysical and electrochemical properties, showing that the intramolecular charge transfer was enhanced. 13 In this communication, we further extended the conjugated system by fusing isoindigo with benzofuran or benzothiophene moiety, and investigated their OFET performance. Since isoindigo core is electron-decient and benzothiophene or benzofuran terminal is electron-rich, it might form an intramolecular Donor-Acceptor-Donor (D-A-D) structure, which we speculated will lead to improved performance.…”

mentioning

confidence: 99%

Extended isoindigo core: synthesis and applications as solution-processable n-OFET materials in ambient conditions

Zheng

et al. 2015

RSC Adv.

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Synthesis of a thiophene-fused isoindigo derivative: a potential building block for organic semiconductors

Cited by 18 publications

References 33 publications

Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

Thiophene-fused isoindigo based conjugated polymers for ambipolar organic field-effect transistors

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Extended isoindigo core: synthesis and applications as solution-processable n-OFET materials in ambient conditions

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